August 23, (THEWILL) — There is an intriguing idea in investing known as the margin of safety. The principle is most closely associated with Benjamin Graham, the legendary investor and teacher of Warren Buffett. At its simplest, it means leaving enough room in a decision for the possibility that your assumptions may be wrong. You do not build a strategy that succeeds only if everything unfolds exactly as expected.
You allow for uncertainty, miscalculation and the inconvenient reality that even very good judgement is sometimes imperfect.
We golfers have our own version of the same principle. We call it “playing the miss.”
It sounds almost contradictory. Surely the object of golf is to hit the shot you want, not plan for the one you do not. Yet one of the distinctions between thoughtful course management and simply hitting golf balls is understanding that the intended shot is only one possible outcome.
For those less familiar with the game, course management is essentially the strategic side of golf: Deciding where to aim, which club to use, which hazards to avoid and how much risk a particular situation justifies. It is not simply about whether you can execute a shot, but whether you should attempt it in the first place.
Every golfer has tendencies. One player typically misses to the right; another tends to pull the ball on the left . The better players know their patterns intimately. They stand over a shot fully intending to execute it perfectly, but somewhere in their calculations sits another, quieter question: If I don’t, where is the safest place to miss?
For my non-golfer readers, imagine a hole where the flag marking the target sits towards the left side of the green, very close to a deep sand bunker. If you have been following this page, you should be familiar with greens and sand traps by now. There is plenty of room on the green to the right. The spectacular shot is to aim directly at the flag; the intelligent shot may be to aim several metres to the right.
Hit it perfectly and you still have a reasonable opportunity to complete the hole well; miss slightly and you remain safe. Aim aggressively at the flag, however, and an ordinary error could leave you in serious trouble. The difference is subtle but profound. In one case, your plan assumes perfection. In the other, your plan accommodates humanity. Professional golfers understand this extraordinarily well. Television can create the impression that the world’s best players attack every flag simply because they possess the skill to do so. In reality, elite golf is deeply strategic.
At the 2026 Open Championship at Royal Birkdale, Jon Rahm spoke about adapting his strategy to the firm conditions, including accepting his caddie’s advice to use a shorter club from the 16th tee than he initially intended. At that level, the question is not simply how far you can hit the ball, but where you want to play the next one from. That is not a lack of ambition. It is sophisticated risk management. Playing the miss does not mean expecting to fail. The golfer still commits fully to the intended shot. It means recognising that confidence and uncertainty can coexist. You can believe strongly in your ability while acknowledging that you will not execute perfectly every time.
I have encountered versions of this repeatedly over nearly three decades in corporate and consulting life. Some of the most important conversations around a strategy are not about the projected returns if everything works, but about what happens if one or two critical assumptions do not. I have sat in rooms where the numbers looked compelling and the opportunity was genuinely exciting, yet the more consequential question was not simply how much could be gained, but how much could be lost if our assumptions proved wrong.
Over time, I have learnt to value the person in the room who asks the uncomfortable question.
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What if revenues come in below projection? What if implementation takes longer? What if a critical partner withdraws or regulation changes? Earlier in my career, I might have regarded some of those questions as excessive caution. Today, I see them differently. They are often what responsible stewardship looks like when other people’s capital, livelihoods and institutions are affected by our decisions.
In many respects, that is simply playing the miss. You pursue the opportunity, but structure the decision so that being slightly wrong does not become catastrophic.
Modern life is filled with applications of the same principle. Engineers build redundancy into critical infrastructure. Financial institutions maintain capital buffers. Prudent investors diversify.
Aircraft have backup systems. Organisations develop succession plans. None exists because failure is desired; they exist because responsible decision-making recognises that things do not always go according to plan.
Fear asks, What if everything goes wrong? Wisdom asks, If something goes wrong, have we left ourselves enough room to recover? That is the essence of margin of safety. The golfer who aims away from the bunker is not conceding defeat to it. He is simply refusing to make his score unnecessarily dependent upon perfection.
Perhaps this is also why experience changes the way many of us approach risk. When we are younger, the most exciting question is often: How much can I gain? With greater responsibility comes another: What must I protect? Wisdom lies in knowing when each question should dominate.
Warren Buffett has built much of his investment philosophy around avoiding permanent loss rather than pursuing every possible gain. His approach reflects Graham’s deeper insight that successful investing is not merely about identifying opportunity; it is also about ensuring that an error in judgement does not become fatal.
Yet there is a danger of taking the idea too far. A life built entirely around avoiding mistakes would become painfully small. Businesses would never innovate, leaders would never attempt difficult reforms, and golfers would never attack a reachable target. Playing the miss is not an invitation to live defensively. It is about choosing risks intelligently.
Good golfers eventually learn something humbling: your best shot tells you what is possible, but your misses often reveal how good your strategy really was. If every imperfect execution produces disaster, the problem may not always be the swing. Sometimes the problem was the target.
This week, consider one important decision before you, whether financial, professional, personal or otherwise. By all means consider what happens if everything goes according to plan, but consider the other possibility too. If your assumptions are slightly wrong, circumstances change or execution is less than perfect, have you left yourself somewhere safe to land? Golf calls it playing the miss. Benjamin Graham called it a margin of safety.
Whatever we choose to call it, wisdom rarely demands perfection. It simply asks us not to make perfection the price of success.
•The author, Meka Niyi Olowola (FSPIN), is a sustainability and communications expert, business leader and avid golfer.
